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Saturday, February 19, 2011


Systematic (IUPAC) name
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)->2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS number 73384-59-5
ATC code J01DD04
PubChem CID 5479530
DrugBank APRD00395
ChemSpider 4586394 YesY
UNII 75J73V1629 YesY
KEGG D07659 YesY
Chemical data
Formula C18H18N8O7S3 
Mol. mass 554.58 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability n/a
Metabolism Negligible
Half-life 5.8–8.7 hours
Excretion 33–67% renal, 35–45% biliary
Therapeutic considerations
Pregnancy cat. B1(AU) B(US)
Legal status Prescription Only (S4) (AU)
Routes Intravenous, intramuscular
 YesY(what is this?)  (verify)
Ceftriaxone (INN) (pronounced /ˌsɛftraɪˈæksoʊn/) is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram-positive and Gram-negative bacteria. In most cases, it is considered to be equivalent to cefotaxime in terms of safety and efficacy. Ceftriaxone sodium is marketed by Hoffman-La Roche under the trade name Rocephin.


  • 1 Clinical use
  • 2 Chemistry

Clinical use

Ceftriaxone is often used (in combination, but not direct, with macrolide and/or aminoglycoside antibiotics) for the treatment of community-acquired or mild to moderate health care-associated pneumonia. It is also a choice drug for treatment of bacterial meningitis. In pediatrics, it is commonly used in febrile infants between 4 and 8 weeks of age who are admitted to the hospital to exclude sepsis. The dosage for acute ear infection in the very young is 50 mg/kg IM, one dose only. It has also been used in the treatment of Lyme disease, typhoid fever and gonorrhea.[citation needed]
Intravenous dosages may be adjusted for body mass in younger patients and is administered every 12–24 hours, at a dose that depends on the type and severity of the infection.
For the treatment of gonorrhea, a single intramuscular injection is usually given. Treatment for chlamydia infection is also recommended (usually with azithromycin) unless it is specifically ruled out.[1]
It must not be mixed or administered simultaneously (within 48 hours) with calcium-containing solutions or products for patients younger than 28 days old,[2] even via different infusion lines (rare fatal cases of calcium-ceftriaxone precipitates in lung and kidneys in neonates have been described).[3]
To reduce the pain of intramuscular injection, ceftriaxone may be reconstituted with 1% lidocaine.[4]
Ceftriaxone has also been investigated for efficacy in preventing relapse to cocaine addiction.[5]


Ceftriaxone is a white crystalline powder which is readily soluble in water, sparingly soluble in methanol and very slightly soluble in ethanol. The pH of a 1% aqueous solution is approximately 6.7.
The syn-configuration of the methoxyimino moiety confers stability to β-lactamase enzymes produced by many Gram-negative bacteria. Such stability to β-lactamases increases the activity of ceftriaxone against otherwise resistant Gram-negative bacteria. In place of the easily hydrolysed acetyl group of cefotaxime, ceftriaxone has a metabolically stable thiotriazinedione moiety.

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